KR20180056314A - Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same - Google Patents

Abstract

Disclosed are an organometallic compound, an organic light-emitting device containing the organometallic compound, and a diagnostic composition containing the organometallic compound. According to the present invention, the organometallic compound exhibits excellent electrical properties and thermal stability.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent device, an organic electroluminescent device including the organic electroluminescent device,

Organic metal compounds, organic light emitting devices including the same, and diagnostic compositions including the organic light emitting devices are disclosed.

BACKGROUND ART An organic light emitting device is a self light emitting type device having excellent viewing angle, response time, luminance, driving voltage, and response speed, and can be multi-colored.

According to an example, the organic light emitting element may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transporting region may be provided between the anode and the light emitting layer, and an electron transporting region may be provided between the light emitting layer and the cathode. The holes injected from the anode move to the light emitting layer via the hole transporting region, and electrons injected from the cathode move to the light emitting layer via the electron transporting region. The holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

On the other hand, a luminescent compound, for example, a phosphorescent luminescent compound can also be used for monitoring, sensing, and detecting biological materials such as various cells and proteins.

A novel organic metal compound, an organic light emitting device employing the same, and a diagnostic composition employing the same.

According to one aspect, there is provided an organometallic compound represented by the following formula:

≪ Formula 1 >

In the above formula

M is at least one selected from the group consisting of beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu) ), Germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt)

X ₁ is O or S, the bond between X ₁ and M is a covalent bond,

X ₂ is N, the bond between X ₂ and M is a coordination bond,

X ₃ and X ₄ independently of one another are C or N,

One of the bonds between X ₃ and M and the bond between X ₄ and M is a covalent bond and the other is a coordinate bond,

Y ₁ to Y ₇ are independently of each other C or N,

Y ₈ and Y ₉ are independently of each other C, N, O or S,

A bond between Y ₁ and Y ₈ or an atomic group and a bond or an atomic group between Y ₁ and Y ₂ constitute CY ₁ and a bond or an atomic group between X ₂ and Y ₃ and a bond or an atomic group between X ₂ and Y ₄ CY ₂ , the bond between X ₃ and Y ₅ or the atomic group and the bond or atomic group between X ₃ and Y ₆ constitute CY ₃ , the bond or atomic group between X ₄ and Y _7, and the bond between X ₄ and Y ₉ Or the atomic group constitutes CY ₄ ,

CY ₁ , CY ₃ and CY ₄ are each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group,

CY ₂ is a group selected from the group consisting of azacarbazole group, azadibenzo boro group, azadibenzophosphole group, azafluorene group, azadibenzosilyl group, azadibenzomol group, Azadibenzothiophene group, azadibenzoselenophen group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group and azadibenzothiophene 5,5 - < / RTI >

T ₁ to T ₃ independently of each _{other, * -N [(L 5)} a5 - (R 5)] - * ', * -B (R 5) - *', * -P (R 5) - * ' _{, * -C (R 5) (} R 6) - * ', * -Si (R 5) (R 6) - *', * -Ge (R 5) (R 6) - * ', * -S- * ', * -Se- *', * -O- * ', * -C (= O) - *', * -S (= O) - * ', * -S (= O) 2 - *' _{, * -C (R 5) =} * ', * = C (R 5) - *', * -C (R 5) = C (R 6) - * ', * -C (= S) - *' And * -C? C- * ',

L ₅ is selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

a5 is 1 to 3 selected from, a5, if 2 or more, two or more of L ₅ are the same or different from each other,

R ₅ and R ₆ are optionally linked to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,

b1 to b3 independently of one another are 0, 1, 2 or 3 and when b1 is 0, * - (T ₁ ) _b1 - * is a single bond, and when b2 is 0 * - (T ₂ ) _b2 - * is a single bond, and when b3 is 0, * - (T ₃ ) _{b 3} - * '

R ₁ to R ₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ arylox group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or non-substituted 1-aromatic-axis A polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q ₇ ) and -P (= O) (Q ₈ ) (Q ₉ )

a1 to a4 are independently of each other 0, 1, 2, 3, 4 or 5,

two of a1 of R ₁ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

two of a2 of R ₂ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

two of a3 of R ₃ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

two of a4 of R ₄ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

Two or more of the neighboring R ₁ to R ₄ may optionally be bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,

One of R ₅ and R ₆ and R ₃ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group You can,

R ₅ and R ₆ and R ₁ , R ₂ , R ₃ or R ₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ Lt; RTI ID = 0.0 > C30 < / RTI _> heterocyclic group,

The substituted C ₅ -C ₃₀ carbocyclic group, a substituted C ₁ -C ₃₀ heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C _A substituted C ₁ -C ₆ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ cycloalkenyl group, -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, , The substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocyclic polycyclic group,

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group And a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, and C _A C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, - _{N (Q 21) (Q 22} ), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q 29) at least one selected from the substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ Group-, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );

≪ / RTI >

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ aryl A C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one of the organometallic compounds.

The organic metal compound in the light emitting layer may serve as a dopant.

According to another aspect, there is provided a diagnostic composition comprising at least one organometallic compound represented by the above formula (1).

The organic metal compound has excellent electrical characteristics and thermal stability. The organic light emitting device employing the organic metal compound has excellent driving voltage, efficiency, power, color purity and lifetime characteristics. In addition, since the organometallic compound has excellent phosphorescent emission characteristics, it can provide a diagnostic composition having a high diagnostic efficiency.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

The organometallic compound is represented by the following Formula 1:

≪ Formula 1 >

M in the chemical formula 1 is at least one selected from the group consisting of beryllium Be, magnesium Mg, aluminum Ca, titanium Ti, manganese Mn, cobalt, (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum ).

For example, M in the above formula (1) may be platinum (Pt), but is not limited thereto.

The organometallic compound represented by the general formula (1) may be neutral not composed of an ion pair of a cation and an anion.

In Formula 1, X ₁ is O or S, and the bond between X ₁ and M may be a covalent bond.

X ₂ in Formula 1 is N, and the bond between X ₂ and M may be a coordination bond.

X ₃ and X ₄ in Formula 1 are independently C or N, one of X ₃ and M and one of X ₄ and M is a covalent bond, and the other is a coordination bond have.

For example, in the formula 1, i) X ₃ is N, the bond between X ₃ and M is a coordinate bond, X ₄ is C, and the bond between X ₄ and M is a covalent bond; Or ii) X ₃ is C, the bond between X ₃ and M is a covalent bond, X ₄ is N, and the bond between X ₄ and M may be a coordination bond.

In Formula 1, Y ₁ to Y ₇ may independently be C or N.

Y ₈ and Y ₉ in Formula 1 may be independently of each other C, N, O, or S.

According to one embodiment, X ₃ in Formula 1 is C, the bond between X ₃ and M is a covalent bond, X ₄ is N, the bond between X ₄ and M is a coordinate bond, Y ₁ to Y ₇ may be C, but is not limited thereto.

A bond between Y ₁ and Y ₈ or an atomic group and a bond or an atomic group between Y ₁ and Y ₂ constitute CY ₁ and a bond or an atomic group between X ₂ and Y ₃ and a bond or an atomic group between X ₂ and Y ₄ CY ₂ , the bond between X ₃ and Y ₅ or the atomic group and the bond or atomic group between X ₃ and Y ₆ constitute CY ₃ , the bond or atomic group between X ₄ and Y _7, and the bond between X ₄ and Y ₉ bond or an atomic group between may configure CY _4.

CY ₁ , CY _3, and CY ₄ in Formula 1 may be independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group.

For example, CY ₁ , CY _3, and CY ₄ in Formula 1 may be independently selected from 6-membered ring groups.

As another example, CY ₁ , CY ₃ and CY ₄ in the above formula (1) are, independently from each other, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, Group, a 1,2,3,4-tetrahydronaphthalene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzophenol group, a benzophorpol group, , A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, Group, dibenzothiophene group, dibenzoselenophen group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5- Carbazole group, azadibenzo borole group, azadibenzofospor group , Azafluorene group, azadibenzoylsilyl group, azadibenzoylmol group, azadibenzothiophene group, azadibenzoselenophen group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza- 9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group , Quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, tetrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, A thiazole group, a benzothiazole group, a benzothiazole group, a 5,6,7,8-tetrahydroisoquinoline (5 , 6,7,8-tetrahydroisoquinoline) group and 5,6,7 , 8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline), but is not limited thereto.

As another example, CY ₁ , CY ₃ and CY ₄ in the above formula (1) are, independently from each other, a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, An azabenzothiophene group, an azabibenzosilyl group, an azabibenzoselenophen group, an azabenzene group, an azabenzene group, a dibenzoselenophen group, an azafluorene group, an azacavazole group, an azabibenzofuran group, 4-tetrahydronaphthalene, pyridine group, pyrimidine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, 5,6,7,8-tetrahydroiso But are not limited to, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

CY ₂ in the above formula (1) may be at least one group selected from the group consisting of azacavazole group, azadibenzo boro group, azadibenzophosphole group, azafluorene group, azadibenzosilyl group, Azodibenzothiophene group, azadibenzothiophene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene group, Lt; / RTI > 5,5-dioxide group.

In the present specification, the terms "azacibazole group, azadibenzo borole group, azadibenzofospor group, azafluorene group, azadibenzosilyl group, azadibenzotomole group, azadibenzothiophene group, azadibenzosele Azaindibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group and azadibenzothiophene 5,5-dioxide group "are each referred to as" carbazole group , A dibenzoylborane group, a dibenzofurane group, a dibenzofurane group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, Group, " 9H-fluorene-9-one group and dibenzothiophene 5,5-dioxide group " means a heterocycle having at least one of the carbons forming the ring thereof substituted with nitrogen do.

For example, CY ₂ in the above formula (1) may be an azacarbazole group, an azafluorene group, an azadibenzosilyl group, an azadibenzothiophene group , Azadibenzoselenophen group, azadibenzofuran group, and azadibenzothiophene, but the present invention is not limited thereto.

In the formula 1 T ₁ to T ₃ independently of each _{other, * -N [(L 5)} a5 - (R 5)] - * ', * -B (R 5) - *', * -P (R 5 ) - * ', * -C ( R 5) (R 6) - *', * -Si (R 5) (R 6) - * ', * -Ge (R 5) (R 6) - *', -S (= O) -, -S (= O) -, -S (= O) _{2 - * ', * -C (} R 5) = *', * = C (R 5) - * ', * -C (R 5) = C (R 6) - *', * -C (= S ) - * ' and * -C [identical to] C- *. The description of R ₅ and R ₆ is given below.

Wherein L ₅ is selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, and a5 is selected from 1 to 3 g., a5 is Yes 1 il), a5 may, if 2 or more, two or more of L ₅ are the same or different from each other.

According to one embodiment, L < ₅ >

A phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrimidinylene group and a carbazolylene group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, A phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrimidinylene group and a carbazolylene group which are substituted with at least one selected from a biphenyl group and a terphenyl group;

, But is not limited thereto.

According to one embodiment, the formula of which is independently from each other T ₁ to _{T 3, * -N [(L} 5) a5 - (R 5)] - * ', * -C (R 5) (R 6) - * ', * -Si (R ₅ ) (R ₆ ) - *', * -S- * 'and * -O- *'.

R ₅ and R ₆ are optionally linked to each other through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group A 5 to 7-membered cyclic group having 5 or 6 carbon atoms or a 5 to 6 membered cyclic group substituted with at least one of deuterium, cyano group, -F, C ₁ -C ₁₀ alkyl group and C ₆ -C ₁₄ aryl group, 5-membered to 7-membered cyclic group of the formula (I).

According to one embodiment, T ₁ to T ₃ independently of one another are * -C (R ₅ ) (R ₆ ) - * ', * -Si (R ₅ ) (R ₆ ) (R ₅ ) (R ₆ ) - * ',

And R ₅ and R ₆ are connected to each other through a first connector,

The first connector is a single _{bond, * -N [(L 9)} a9 - (R 9)] - * ', * -B (R 9) - *', * -P (R 9) - * ', _{* -C (R 9) (R} 10) - * ', * -Si (R 9) (R 10) - *', * -Ge (R 9) (R 10) - * ', * -S- * ', * -Se- *', * -O- * ', * -C (= O) - *', * -S (= O) - * ', * -S (= O) 2 - *', _{* -C (R 9) = *} ', * = C (R 9) - *', * -C (R 9) = C (R 10) - * ', * -C (= S) - *' and * -C? C- * ',

Each of R ₉ and R ₁₀ is described with reference to R ₅ in the present specification,

For the description of L ₉ , refer to the description of L ₅ in the present specification,

The description of a9 refers to the description of a5 in the first paragraph,

* And * may be, independently of each other, a bonding site with neighboring atoms, but are not limited thereto.

B1 to b3 in the above formula (1) represent the number of T ₁ to T ₃ , and independently of each other, may be 0, 1, 2 or 3. If b1 is 0, _{* - (T 1) b1 -} * ' case is a single bond, b2 is 0, _{* - (T 2) b2 -} *' case is a single bond, b3 is 0, * - ( T ₃ ) _{b 3} - * 'may be a single bond.

According to one embodiment, in Formula 1,

b1, b2 and b3 are 0;

b1 is 1, b2 and b3 are 0;

b2 is 1, b1 and b3 are 0; or

b3 is 1, and b1 and b2 may be 0, but the present invention is not limited thereto.

In Formula 1, R ₁ to R ₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amidino group, , A hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, hwandoen C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ ring - C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1 (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) (Q ₅ ), - (substituted or unsubstituted) monovalent non-aromatic heterocyclic polycyclic groups, B may be selected from (Q ₆₎ (Q _7), and _{-P (= O) (Q 8} ) (Q 9).

For example, R ₁ to R ₆ , independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, An adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one;

A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A phenyl group, a pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, an imidazolyl group, an imidazolyl group, a pyrazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, A quinolinyl group, a quinolizinyl group, a quinazolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazole group, a benzoquinolyl group, a benzoquinolinyl group, A benzooxazolyl group, a benzoxazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyridinyl group, A diazopyrimidinyl group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, A cycloheptenyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a naphthyl group, a naphthyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, , Isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, , An indolyl group, an indolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, A benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofurano group, A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group substituted with at least one member selected from a phenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group a cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthene group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyrimidyl group, a pyridyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, A benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And

_{-N (Q 1) (Q 2} ), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );

≪ / RTI >

Q ₁ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

As another example, R ₁ to R ₆ , independently of each other,

An alkyl group having 1 to 10 carbon atoms which may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , methyl, ethyl, n-propyl, isopropyl, An n-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an isobutyl group, an isobutyl group, , a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secononyl group, A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, A norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, A dibenzothiophenyl group;

Heavy _{hydrogen, -F, -CD 3, -CD 2} H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, cyano, nitro, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy A cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, An ethyl group, an n-propyl group, an isopropyl group, an isopropyl group, an isopropyl group, a n-butyl group, a n-butyl group, a n-butyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, A tert-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, heptyl group, n-octyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, isohexyl group, , sec-nonyl group, tert-nonyl group, n- A cyclohexyl group, a cycloheptyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzyl group, a naphthyl group, A benzofuranyl group and a dibenzothiophenyl group; And

_{-N (Q 1) (Q 2} ), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );

≪ / RTI >

Descriptions of Q ₁ through Q ₉ can be referred to those described herein.

According to one embodiment, R ₁ to R ₆ independently of one another are hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH _{2 , -CF 3, -CF 2 H,} -CFH 2, to groups and -Si (Q ₃₎ is displayed to the group, of the formula 9-1 to 9-19 by the general formula 10-1 to 10-142 (Q ₄ ) (Q ₅ ) wherein the description of Q ₃ to Q ₅ are each as set forth herein:

In the above formulas (9-1) to (9-19) and (10-1) to (10-142), * denotes a binding site with neighboring atoms, Ph denotes a phenyl group, and TMS denotes a trimethylsilyl group.

A1 to a4 in the formula (1) represent the number of R ₁ to R ₄ , and may be independently 0, 1, 2, 3, 4 or 5. The a1 is 2, if greater, may be two or more of R ₁ are the same or different from each other, if the a2 is 2 or greater, it is possible to two or more of R ₂ are the same or different from each other, when the a3 is 2 or more, two or more of R ₃ may be the same as or different from each other, and when a4 is at least 2, at least two R ₄ may be the same or different, but are not limited thereto.

In Formula 1, two of the three a1 R ₁ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, may form, two of a2 of R ₂ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, may form, two of a3 of R ₃ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, may form, two of a4 of R ₄ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, It may form, R ₁ to R ₄ of the neighboring two or more optionally, in combination with each other, substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ may form a heterocyclic ring group, R ₅ and R ₆ and one of R ₃ are, optionally, bonded to each other, substituted Or an unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, and one of R ₅ and R ₆ and R ₄ can optionally form a To form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group.

For example, the general formula (2) of i) a1 of R ₁ of 1, ii) two of a2 of R _2, iii) two of a3 of R _3, two of iv) a4 of R ₄ dogs, v) the R ₁ to R ₄ of the neighboring two or more, vi) R ₅ and R ₆ a and R of _3, and vii) R ₅ and R ₆ and one R ₄ wherein each Alternatively, the bond to one another, which can form , A substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

A cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, , Naphthalene group, anthracene group, tetracene group, phenanthrene group, dihydronaphthalene group, phenalene group, benzothiophene group, benzofuran group, indene group, indole group, benzoylol group, azabenzothiophene group, A benzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

A cyclohexane group, a cycloheptane group, an adamantane group, a bicycle-heptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyridine group substituted with at least one R _1a , A benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, an imine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, Group, an azabenzothiophene group, an azabenzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

, But is not limited thereto.

For a description of R _1a , refer to the description of R ₁ in the present specification.

로 표시되는 모이어티는 하기 화학식 CY1-1 내지 CY1-16로 표시되는 그룹 중에서 선택될 수 있다:According to one embodiment,

May be selected from the group represented by the following formulas CY1-1 to CY1-16:

Among the above-mentioned formulas CY1-1 to CY1-16

And X ₁₁ is N or C (R _11), X ₁₂ is N or C (R _12), and, X ₁₃ is N or C (R _13), and, X ₁₄ is N or C (R _14), X ₁₅ a is N or C (R _15), and, X ₁₆ is N or C (R _16), and, X ₁₇ is N or C (R _17), and, X ₁₈ is N or C (R _18),

X ₁₉ is C (R _19a ) (R _19b ), N (R ₁₉ ), O, S or Si (R _19a ) (R _19b )

R ₁₁ to R ₁₉ and R _19a to R _19c independently of each other, refer to the description of R ₁ in the present specification,

* And * are independent sites of bonding to neighboring atoms.

For example, In the formula CY1-1 CY1-16 to X ₁₁ are C (R _11), and, X ₁₂ is C (R _12), and, X ₁₃ is C (R _13), and, X ₁₄ is C (R ₁₄ ), X ₁₅ is C (R ₁₅ ), X ₁₆ is C (R ₁₆ ), X ₁₇ is C (R ₁₇ ), and X ₁₈ is C (R ₁₈ ) no.

로 표시되는 모이어티가 하기 화학식 CY2-1 내지 CY2-4로 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment,

May be selected from the group represented by the following formulas CY2-1 to CY2-4:

Among the above-mentioned formulas CY2-1 to CY2-4

And X ₂₁ is N or C (R _21), X ₂₂ is N or C (R _22), and, X ₂₃ is N or C (R _23), and, X ₂₄ is N or C (R _24), and, X ₂₅ Is N or C (R < ₂₅ >),

X ₂₉ is C (R _29a ) (R _29b ), N (R ₂₉ ), O, S or Si (R _29a ) (R _29b )

R ₂₁ to R ₂₅ , R ₂₉ and R _29a to R _29c are independently of each other, with reference to the description of R ₂ in the present specification,

*, *, And * are independent sites of bonding to neighboring atoms.

For example, if X ₂₁ is N or C (R ₂₁₎ In the formula CY2-1 to CY2-4, X ₂₂ is N or C (R _22), X ₂₃ is a C (R _23), X ₂₄ Is C (R ₂₄ ), and X ₂₅ is C (R ₂₅ ), but is not limited thereto.

로 표시되는 모이어티는 하기 화학식 CY3-1 내지 CY3-22로 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment,

May be selected from the group represented by the following formulas CY3-1 to CY3-22:

Among the above-mentioned formulas CY3-1 to CY3-22

And X ₃₁ is N or C (R _31), X ₃₂ is N or C (R _32), and, X ₃₃ is N or C (R _33), and, X ₃₄ is N or C (R _34), and, X ₃₅ Is N or C (R ₃₅ ), X ₃₆ is N or C (R ₃₆ ), X ₃₇ is N or C (R ₃₇ )

X ₃₉ is a _{C (R 39a) (R 39b} ), N (R 39), O, S , or _{Si (R 39a) (R 39b} ),

R ₃₁ to R ₃₉ and R _39a to R _39b are independently of each other, with reference to the description of R ₃ in the present specification,

*, *, And * are independent sites of bonding to neighboring atoms.

For example, in the above formulas CY3-1 to CY3-22, X ₃₁ is C (R ₃₁ ), X ₃₂ is C (R ₃₂ ), X ₃₃ is C (R ₃₃ ), X ₃₄ is C ₃₄ ), X ₃₅ is C (R ₃₅ ), X ₃₆ is C (R ₃₆ ), and X ₃₇ is C (R ₃₇ ).

로 표시되는 모이어티는 하기 화학식 CY4-1 내지 CY4-8 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment,

May be selected from the group represented by the following formulas CY4-1 to CY4-8:

Among the above-mentioned formulas CY4-1 to CY4-8

And X ₄₁ is N or C (R _41), X ₄₂ is N or C (R _42), and, X ₄₃ is N or C (R _43), and, X ₄₄ is N or C (R _44), X ₄₅ Is N or C (R ₄₅ ), X ₄₆ is N or C (R ₄₆ ), X ₄₇ is N or C (R ₄₇ ), X ₄₈ is N or C (R ₄₈ )

R ₄₁ to R ₄₈ independently of one another, with reference to the description of R ₄ in this specification,

* And * are independent sites of bonding to neighboring atoms.

For example, the formula CY4-1 to CY4-8 of X ₄₁ are C (R _41), and, X ₄₂ is C (R _42), and, X ₄₃ is C (R _43), and, X ₄₄ is C (R ₄₄ ), X ₄₅ is C (R ₄₅ ), X ₄₆ is C (R ₄₆ ), X ₄₇ is C (R ₄₇ ), and X ₄₈ is C (R ₄₈ ) no.

According to another embodiment, in Formula 1,

로 표시되는 모이어티는 상기 화학식 CY1-1 및 CY1-5 내지 CY1-10으로 표시되는 그룹 중에서 선택되고,

Is selected from the group represented by the above formulas CY1-1 and CY1-5 to CY1-10,

로 표시되는 모이어티는 상기 화학식 CY2-1 내지 CY2-4로 표시되는 그룹 중에서 선택되고,

Is selected from the group represented by the above formulas CY2-1 to CY2-4,

로 표시되는 모이어티는 상기 화학식 CY3-1 및 CY3-4 내지 CY3-11로 표시되는 그룹 중에서 선택되고,

Is selected from the group represented by the above formulas CY3-1 and CY3-4 to CY3-11,

로 표시되는 모이어티는 상기 화학식 CY4-1로 표시되는 그룹 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다.

May be selected from the group represented by the above formula (CY4-1), but the present invention is not limited thereto.

According to another embodiment, in Formula 1,

CY1 is selected from the group consisting of the following formulas CY1 (1) to CY1 (9)

CY2 is selected from the group consisting of the following formulas CY2-1 to CY2-4,

CY3 is selected from the group consisting of the following formulas CY3 (1) to CY3 (14)

CY4 can be selected from the group consisting of the following groups represented by the following formulas CY4 (1) to CY4 (9), but is not limited thereto:

The description of R ₁₁ to R ₁₄ in the above formulas CY1 (1) to CY1 (9) will be described with reference to R ₁ in the present specification, wherein R ₁₁ to R ₁₄ are not hydrogen,

And X ₂₁ is N or C (R ₂₁₎ In the formula CY2-1 to CY2-4, X ₂₂ is N or C (R _22), and, X ₂₃ is C (R _23), and, X ₂₄ is C (R ₂₄ ), X ₂₅ is C (R ₂₅ )

X ₂₉ is C (R _29a ) (R _29b ), N (R ₂₉ ), O, S or Si (R _29a ) (R _29b )

R ₂₁ to R ₂₅ , R ₂₉ and R _29a to R _29c are independently of each other, with reference to the description of R ₂ in the present specification,

In the formula, CY3 (1) to CY3 (14) X ₃₉ are _{C (R 39a) (R 39b} ), N (R 39), O, S , or _{Si (R 39a) (R 39b} ) , and, R ₃₁ to R ₃₃ , R ₃₉ , R _39a and R _39b are each referred to in the description of R ₃ in the specification, wherein R ₃₁ to R ₃₃ are not hydrogen,

The description of R ₄₁ to R ₄₄ in the formulas CY4 (1) to CY4 (9) will be described with reference to R ₄ in the present specification, wherein R ₄₁ to R ₄₄ are not hydrogen,

*, * And * in the above formulas CY (1) to CY (9), CY2-1 to CY2-4, CY3 (1) to CY3 (14) and CY4 It is a binding site with one atom.

According to another embodiment, the organometallic compound may be represented by one of the following formulas 1-1 to 1-4:

Among the above formulas 1-1 to 1-4

M, X ₁ , T ₁ to T _3, and b ₁ to b ₃ respectively refer to those described in this specification,

Wherein X ₁₁ is N or C (R ₁₁ ), X ₁₂ is N or C (R ₁₂ ), X ₁₃ is N or C (R ₁₃ ), X ₁₄ is N or C (R ₁₄ )

And X ₂₁ is N or C (R _21), X ₂₂ is N or C (R _22), and, X ₂₃ is N or C (R _23), and, X ₂₄ is N or C (R _24), and, X ₂₅ Is N or C (R < ₂₅ >),

X ₃₁ is N or C (R ₃₁ ), X ₃₂ is N or C (R ₃₂ ), X ₃₃ is N or C (R ₃₃ )

And X ₄₁ is N or C (R _41), X ₄₂ is N or C (R _42), and, X ₄₃ is N or C (R _43), and, X ₄₄ is N or C (R _44),

R ₁₁ to R ₁₄ are independently of each other, with reference to the description of R ₁ in the present specification, and two of R ₁₁ to R ₁₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

R ₂₁ to R ₂₅ are independently of each other, with reference to the description of R ₂ in the present specification, and _two of R ₂₁ to R ₂₅ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

The description of R ₃₁ to R ₃₃ independently of each other refers to the description of R ₃ in the present specification, and two of R ₃₁ to R ₃₃ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

The description of R ₄₁ to R ₄₄ independently of each other refers to the description of R ₄ in the present specification, and two of R ₄₁ to R ₄₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group.

For example, in the above formulas 1-1 to 1-4, X ₁₁ is C (R ₁₁ ), X ₁₂ is C (R ₁₂ ), X ₁₃ is C (R ₁₃ ), X ₁₄ is C R ₁₄₎ and, wherein X ₂₁ is N or C (R _21), X ₂₂ is C (R _22), and X ₂₃ are C (R _23), and X ₂₄ are C (R _24), X ₂₅ is C (R _25), and, X ₃₁ is C (R _31), and, X ₃₂ is C (R _32), and, X ₃₃ is C (R _33), and, X ₄₁ is C (R _41), and, X ₄₂ is C (R ₄₂ ), X ₄₃ is C (R ₄₃ ), and X ₄₄ is C (R ₄₄ ), but is not limited thereto.

As another example, in the above formulas 1-1 to 1-4, i) two of R ₁₁ to R ₁₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted Or unsubstituted C ₁ -C ₃₀ heterocyclic group, ii) two of R ₂₁ to R ₂₅ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, Iii) a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group formed by bonding two of R ₃₁ to R ₃₃ to each other to form a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; And iv) two of R ₄₁ to R ₄₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, The substituted C ₁ -C ₃₀ heterocyclic group is, independently of each other,

A cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, , Naphthalene group, anthracene group, tetracene group, phenanthrene group, dihydronaphthalene group, phenalene group, benzothiophene group, benzofuran group, indene group, indole group, benzoylol group, azabenzothiophene group, A benzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

A cyclohexane group, a cycloheptane group, an adamantane group, a bicycle-heptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyridine group substituted with at least one R _1a , A benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, an imine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, Group, an azabenzothiophene group, an azabenzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

, But is not limited thereto.

For a description of R _1a , refer to the description of R ₁ in the present specification.

According to yet another embodiment, the formula 1-1 to 1-4 of the T ₃ is * -N (R ₅₎ - a * 'and, b3 is 1, X ₄₁ is C (R _41), and R ₅ R ₄₁ may be bonded to each other through a single bond (for example, see the following Chemical Formula 1 (1)).

According to another embodiment, the organometallic compound may be represented by one of the following formulas (1) and (2):

In the above formulas (1) and (2)

The descriptions of M, X ₁ to X ₄ , Y ₁ to Y ₉ , CY ₁ to CY ₄ , T ₁ to T ₃ , b ₁ to b ₃ , R ₁ to R ₄ and a ₁ to a ₄ are respectively the same as those described herein See,

X ₄₂ is N or C (R ₄₂ ), X ₄₃ is N or C (R ₄₃ ), X ₄₄ is N or C (R ₄₄ )

The description of R ₄₂ to R ₄₄ independently of each other refers to the description of R ₄ in the present specification, and two of R ₄₂ to R ₄₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

CY ₅ and CY ₆ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

R ₅₁ and R ₆₁ are independently of each other, with reference to the description of R ₁ in this specification,

a51 and a61 are, independently of each other, 0, 1, 2 or 3,

T ₄ is C, Si or Ge,

T ₅ is a single _{bond, * -N [(L 7)} a7 - (R 7)] - * ', * -B (R 7) - *', * -P (R 7) - * ', * -C _{(R 7) (R 8)} - * ', * -Si (R 7) (R 8) - *', * -Ge (R 7) (R 8) - * ', * -S- *', * -Se- * ', * -O- *' , * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C _{(R 7) = * ',} * = C (R 7) - *', * -C (R 7) = C (R 8) - * ', * -C (= S) - *' and * -C ≡C- * ',

The description of R ₇ and R ₈ is the same as the description of R ₅ in the first embodiment,

L ₇ refers to the description of L ₅ in the first paragraph,

a7 refers to the description of a5 in the first paragraph,

* And * are independent sites of bonding to neighboring atoms.

For example, in the above formula (1), X ₄₂ may be C (R ₄₂ ), X ₄₃ may be C (R ₄₃ ), and X ₄₄ may be C (R ₄₄ ), but the present invention is not limited thereto.

As another example, i) two of R ₄₂ to R ₄₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ when heterocyclic group, ii) and iii CY ₅₎ CY ₆ are, independently of each other,

A cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, , Naphthalene group, anthracene group, tetracene group, phenanthrene group, dihydronaphthalene group, phenalene group, benzothiophene group, benzofuran group, indene group, indole group, benzoylol group, azabenzothiophene group, A benzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

A cyclohexane group, a cycloheptane group, an adamantane group, a bicycle-heptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyridine group substituted with at least one R _1a , A benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, an imine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, Group, an azabenzothiophene group, an azabenzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

, But is not limited thereto.

For a description of R _1a , refer to the description of R ₁ in the present specification.

The organometallic compound may be selected from the following compounds 1 to 240, but is not limited thereto:

Wherein X ₂ in Formula 1 is N, and CY ₂ is at least one group selected from the group consisting of azacavazole group, azadibenzo boro group, azadibenzofospor group, azafluorene group, azadibenzo group, Azaindibenzothiophene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group And azadibenzothiophene 5,5-dioxide groups. As a result, the half-width of the emission spectrum of the organometallic compound represented by Formula 1 is reduced, and an electronic device using the organometallic compound represented by Formula 1, for example, an organic light emitting device, have.

For example, the HOMO, LUMO, singlet (S ₁ ) and triplet (T ₁ ) energy levels for compounds 6, 20, 47, 62, 86, 100, 113, 127, The structure is optimized at the level of B3LYP, 6-31G (d, p) using the DFT method of the Gaussian program. The evaluation results are shown in Table 1 below.

Compound No. HOMO (eV) LUMO (eV) S ₁ Energy level (eV) T ₁ energy level (eV) 6 -4.627 -2.034 2.017 1.849 20 -4.516 -2.055 1.901 1.764 47 -4.612 -2.038 1.997 1.828 62 -4.668 -2.030 2.053 1.885 86 -4.790 -1.798 2.461 2.047 100 -4.710 -1.767 2.428 1.993 113 -4.792 -1.802 2.462 2.047 127 -4.765 -1.809 2.423 2.036 170 -4.658 -2.177 1.923 1.780 180 -4.837 -1.914 2.423 1.993 A -4.733 -1.754 2.496 2.208

<Compound A>

It can be seen from the above Table 1 that the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as an electron device, for example, as a dopant of an organic light emitting device.

The method for synthesizing the organometallic compound represented by the above formula (1) can be recognized by those skilled in the art with reference to the following synthesis examples.

Accordingly, the organic metal compound represented by Formula 1 may be suitable for use as an organic layer of an organic light emitting device, for example, as a dopant of a light emitting layer in the organic layer. According to another aspect of the present invention, A second electrode; And an organic layer interposed between the first electrode and the second electrode, the organic layer including a light emitting layer and containing at least one or more organic metal compounds represented by the general formula (1).

The organic light emitting device can have a low driving voltage, a high efficiency, a high power, an elevator efficiency, a long lifetime, a low roll-off ratio, and excellent color purity by providing an organic layer containing an organometallic compound represented by the general formula .

The organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light emitting device. For example, the organic metal compound represented by Formula 1 may be included in the light emitting layer. In this case, the organic metal compound serves as a dopant, and the light emitting layer may further include a host (i.e., the content of the organometallic compound represented by Formula 1 is smaller than the content of the host).

In the present specification, the phrase "(organic layer) contains at least one organometallic compound" means that "(organic layer) contains one organometallic compound belonging to the category of the above formula (1) Or more of the organic metal compound ".

For example, the organic layer may contain only the compound 1 as the organometallic compound. At this time, the compound 1 may exist in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the organometallic compound. At this time, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may exist in the light emitting layer).

The first electrode is a cathode which is a hole injection electrode and the second electrode is a cathode which is an electron injection electrode, or the first electrode is a cathode which is an electron injection electrode and the second electrode is an electron hole injection electrode.

For example, the first electrode of the organic light emitting device may be an anode, the second electrode may be a cathode, and the organic layer may include a hole transporting region interposed between the first electrode and the light emitting layer, Wherein the hole transporting region comprises a hole injecting layer, a hole transporting layer, an electron blocking layer, or any combination thereof, wherein the electron transporting region comprises a hole blocking layer, an electron transporting layer, An electron injection layer, or any combination thereof.

In the present specification, the term " organic layer " refers to a single layer and / or a plurality of layers interposed between the first and second electrodes of the organic light emitting device. The "organic layer" may include not only an organic compound but also an organic metal complex including a metal.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. The organic light emitting diode 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked.

A substrate may further be disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a conventional organic light emitting device can be used. A glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 11 can be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. The first electrode 11 may be an anode. The first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like can be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region; An emission layer; And an electron transport region.

The hole transporting region may be disposed between the first electrode 11 and the light emitting layer.

The hole transporting region may include a hole injecting layer, a hole transporting layer, an electron blocking layer, a buffer layer, or any combination thereof.

The hole transporting region may include only a hole injecting layer, or may include only a hole transporting layer. Alternatively, the hole transporting region may have a structure of a hole injecting layer / a hole transporting layer or a hole injecting layer / a hole transporting layer / an electron blocking layer which are sequentially stacked from the first electrode 11.

When the hole transporting region includes a hole injecting layer, the hole injecting layer (HIL) may be formed on the first electrode 11 by various methods such as a vacuum deposition method, a spin coating method, a casting method, an LB method, have.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, and the like. For example, 500 ℃, the degree of vacuum of about 10 ^-8 to about ¹⁰ can be selected in the range of ³ torr, a deposition rate of about 0.01 to about 100Å / sec, but is not limited to such.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the structure and thermal properties of the compound used as the hole injection layer material, the desired hole injection layer, and the coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for removing the solvent after coating may be selected from the range of about 80 캜 to 200 캜, but is not limited thereto.

The conditions for forming the hole transporting layer and the electron blocking layer refer to conditions for forming the hole injection layer.

NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4 ', 2'- , 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrene sulfonate), Pani / CSA (Polyaniline / Camphor sulfonicacid (Polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 And may include at least one:

&Lt; Formula 201 >

&Lt; EMI ID =

In the above formula (201), Ar ₁₀₁ and Ar ₁₀₂ , independently of each other,

A phenanthrenyl group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, an acenaphthylene group, A phenylene group, a phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non-inde aromatic heterocyclic condensed polycyclic group with at least one substituted phenyl group, a penta-alkylenyl group wherein carbonyl group, a naphthyl group, an azulenyl group, a heptal A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a cyano group, a phenanthrene group, Carbonyl alkylenyl group, a hexenyl group naphtha, blood hexenyl group, a perylenyl group and a carbonyl penta hexenyl groups;

&Lt; / RTI &gt;

In Formula 201, xa and xb may be independently an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R _119, and R ₁₂₁ to R ₁₂₄ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) and C ₁ -C ₁₀ alkoxy group (e.g., methoxy, ethoxy Propoxy group, butoxy group, pentoxy group, etc.);

A sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with one or more of the salts thereof;

A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group substituted with at least one of a salt thereof, a C ₁ -C ₁₀ alkyl group, and a C ₁ -C ₁₀ alkoxy group;

, But is not limited thereto.

In the above formula (201), R &lt; ₁₀₉ &

A phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group;

&Lt; / RTI &gt;

According to one embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but is not limited thereto:

&Lt; Formula 201A >

In the above formula (201A), R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ are described in detail above.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, the following compounds HT1 to HT20:

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the hole transporting region includes at least one of a hole injection layer and a hole transporting layer, the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å To about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. When the thicknesses of the hole transporting region, the hole injecting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

In addition to the materials described above, the hole transporting region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the following compounds HT-D1 and the like, but are not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transporting region may further include a buffer layer.

The buffer layer may serve to increase the efficiency by compensating the optical resonance distance according to the wavelength of the light emitted from the light emitting layer.

A light emitting layer (EML) may be formed on the hole transporting region by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

Meanwhile, when the hole transporting region includes an electron blocking layer, the electron blocking layer material may be selected from a material that can be used in the hole transporting region as described above and a host material described below, but is not limited thereto . For example, when the hole transporting region includes an electron blocking layer, mCP described later can be used as the electron blocking layer material.

The light emitting layer may include a host and a dopant, and the dopant may include an organometallic compound represented by the general formula (1).

The host may comprise at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, Mcp,

<mCP> <Compound H50>            <Compound H51>

Alternatively, the host may further comprise a compound represented by Formula 301:

&Lt; Formula 301 >

In Formula 301, Ar ₁₁₁ and Ar ₁₁₂ are, independently from each other,

A phenylene group, a naphthylene group, a phenanthrenylene group and a pyrenylene group; And

A phenylene group, a naphthylene group, a phenanthrenylene group and a pyrenylene group which are substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group;

&Lt; / RTI &gt;

In Formula 301, each of Ar ₁₁₃ to Ar ₁₁₆ independently represents,

A C ₁ -C ₁₀ alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group and a pyrenyl group; And

A phenyl group, a naphthyl group, a phenanthrenyl group and a pyrenyl group substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group;

&Lt; / RTI &gt;

G, h, i, and j in Formula 301 may be independently an integer of 0 to 4, for example, 0, 1, or 2.

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ independently represent,

A C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group and an anthracenyl group;

A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group which are substituted with at least one of a fluorenyl group and a fluorenyl group; And

;

;

, But is not limited thereto.

Alternatively, the host may comprise a compound represented by Formula 302:

&Lt; Formula 302 >

Of the above formula 302, Ar ₁₂₂ To Ar &lt; ₁₂₅ &gt; refer to the description of Ar &lt; ₁₁₃ &gt; in the above formula (301).

Ar ₁₂₆ and Ar ₁₂₇ in the formula (302) may be, independently of each other, a C ₁ -C ₁₀ alkyl group (for example, a methyl group, an ethyl group or a propyl group).

And k and l in Formula 302 may be independently an integer of 0 to 4. For example, k and l may be 0, 1 or 2.

The compound represented by Formula 301 and the compound represented by Formula 302 may include the following compounds H1 to H42, but are not limited thereto.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the above-described range, it is possible to exhibit excellent light-emitting characteristics without substantial increase in driving voltage.

Next, an electron transporting region is disposed above the light emitting layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

For example, the electron transporting region may have a structure of a hole blocking layer / electron transporting layer / electron injecting layer or electron transporting layer / electron injecting layer, but is not limited thereto. The electron transporting layer may have a single layer or a multi-layer structure including two or more different materials.

The forming conditions of the hole blocking layer, the electron transporting layer and the electron injecting layer in the electron transporting region refer to the forming conditions of the hole injecting layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, but is not limited to, at least one of BCP, Bphen, and Balq.

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

The electron transport layer may further include at least one of the BCP, Bphen and to Alq _3, Balq, TAZ and NTAZ.

Alternatively, the electron transporting layer may include at least one of the following compounds ET1 and ET2, but is not limited thereto.

The thickness of the electron transporting layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transporting layer satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

The electron transporting layer may further include a metal-containing material in addition to the above-described materials.

The metal-containing material may comprise a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may also include an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O and BaO.

The thickness of the electron injection layer may be from about 1 A to about 100 A, e.g., from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

A second electrode 19 is formed on the organic layer 15. The second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- And may be used as a material for forming the second electrode 19. Alternatively, the transmissive second electrode 19 can be formed using ITO or IZO to obtain a front light emitting element.

The organic light emitting device has been described above with reference to FIG. 1, but the present invention is not limited thereto.

According to another aspect, there is provided a diagnostic composition comprising at least one organometallic compound represented by the above formula (1).

Since the organometallic compound represented by Formula 1 can provide high luminous efficiency, the diagnostic composition containing the organometallic compound can have a high diagnostic efficiency.

The diagnostic composition can be applied to a variety of diagnostic kits, diagnostic reagents, biosensors, biomarkers, and the like.

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, A tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the above C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group means a monovalent group having the formula: -OA ₁₀₁ (wherein A ₁₀₁ is the above C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, Isopropyloxy group and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure containing at least one carbon-carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, . In the present specification, the C ₂ -C ₆₀ alkenylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, the C ₂ -C ₆₀ alkynyl group has a structure containing at least one carbon-carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl, propynyl propynyl), and the like. In the present specification, the C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, Tyl group and the like. The C ₃ -C ₁₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₁₀ cycloalkyl group means a group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom, Specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as the above-mentioned C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group means a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring, but does not have aromaticity , And specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, Lt; RTI ID = 0.0 &gt; a &lt; / RTI &gt; Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group means a carbamoyl group having 6 to 60 carbon atoms Quot; means a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group and the like. The C ₆ -C ₆₀ aryl groups and C ₆ -C ₆₀ aryl If the alkylene group contains two or more rings, the two or more rings may be fused to each other.

In the present specification, the C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom and having a cyclic aromatic system having 1 to 60 carbon atoms C ₁ -C ₆₀ heteroarylene group means a bivalent group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms it means. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused together.

In the present specification, the C ₆ -C ₆₀ aryloxy group indicates -OA ₁₀₂ (wherein A ₁₀₂ is the C ₆ -C ₆₀ aryl group), the C ₆ -C ₆₀ arylthio is -SA ₁₀₃ , And A ₁₀₃ is the above C ₆ -C ₆₀ aryl group.

In the present specification, a monovalent non-aromatic condensed polycyclic group is a condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom, and the whole molecule is a non-aromaticity. (E. G., Having from 8 to 60 carbon atoms). Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a condensed heteropolycyclic group in which two or more rings are condensed with each other and a hetero atom selected from N, O, P, Si and S (For example, having from 1 to 60 carbon atoms) having a non-aromaticity throughout the molecule. The monovalent non-aromatic heterocyclic polycyclic group includes a carbazolyl group and the like. In the present specification, the divalent non-aromatic heterocyclic polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, a C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as a ring forming atom. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

In the present specification, a C ₁ -C ₃₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si and S in addition to 1 to 30 carbons as a ring forming atom. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group.

The substituted C ₅ -C ₃₀ carbocyclic group, the substituted C ₂ -C ₃₀ heterocyclic group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C _A substituted C ₁ -C ₆ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ cycloalkenyl group, -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, , The substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocyclic polycyclic group,

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 11) (Q} 12), -Si (Q 13) (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group And a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q _A C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group substituted with at least one selected from the group consisting of a C ₁ -C ₁₀ cycloalkyl group, , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic A heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );

&Lt; / RTI &gt;

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

Hereinafter, compounds and organic light emitting devices according to one embodiment of the present invention will be described in more detail with reference to the following Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

 [Example]

Synthetic example  1: Synthesis of Compound 20

Synthesis of intermediate L1-1

2,4-dichloro-benzo Pew as [3,2-d] pyrimidine (4.79 g, 20.04 mmol), Intermediate L1-2 (8.89 g, 21.04 mmol) , Pd (PPh 3) 4 (1.16 g, 1.00 mmol ) And potassium carbonate (8.31 g, 60.13 mmol) were placed in 200 mL of toluene, and the mixture was stirred under reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature. Thereafter, the reaction mixture was extracted with water and methylene chloride, the solvent was removed, and column chromatography was performed under the condition of hexane: acetylacetate = 8: 2 to obtain 5.22 g (52%) of intermediate L1-1. The material was identified by HPLC analysis.

Synthesis of intermediate L1

3,5-di-tert-butyl-2-hydroxyphenylboronic acid (3.93 g, 15.70 mmol) L1-1 (5.22 g, 10.47 mmol) , Pd (PPh 3) 4 (0.61 g, 0.52 mmol) and potassium carbonate (4.34 g, 31.40 mmol) into a tetrahydrofuran 90mL / 30mL water followed by stirring under reflux for 12 hours After the reaction was completed, the temperature was lowered to room temperature. Thereafter, the reaction mixture was extracted with water and methylene chloride, the solvent was removed, and column chromatography was performed under the condition of hexane: acetylacetate = 85:15 to obtain 4.00 g (57%) of Intermediate L1. The material was identified by HPLC analysis.

Synthesis of Compound 20

The reaction was carried out by mixing the intermediate L1 (1.55 g, 2.32 mmol), PtCl ₂ (NCPh) ₂ (1.21 g, 2.55 mmol) and 20 mL of benzonitrile under refluxing for 12 hours, . After removing the solvent from the mixture obtained therefrom, column chromatography was performed under the condition of hexane: methylene chloride = 7: 3 to obtain 0.54 g (27%) of Compound 20. Mass and HPLC analysis confirmed the material.

_{HRMS (MALDI) calcd for C 45} H 38 N 4 O 2 Pt: m / z 861.2643, Found: 861.2649

Synthetic example  2: Synthesis of compound 47

Synthesis of Intermediate L2-1

2,4-dichloro-benzo Pew as [3,2-d] pyrimidine (3.48 g, 14.55 mmol), Intermediate L2-2 (9.33 g, 15.28 mmol) , Pd (PPh 3) 4 (0.84 g, 0.73 mmol ) And potassium carbonate (6.03 g, 43.65 mmol) were added to 200 mL of toluene, and the mixture was stirred under reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature. Thereafter, the reaction mixture was extracted with water and methylene chloride, the solvent was removed, and column chromatography was performed under the condition of hexane: acetylacetate = 8: 2 to obtain 6.50 g (65%) of intermediate L2-1. The material was identified by HPLC analysis.

Synthesis of Intermediate L2

2-hydroxyphenyl Boro Nick Acid (1.94 g, 14.10 mmol), Intermediate L2-1 (6.46 g, 9.40 mmol) , Pd (PPh 3) 4 (0.54 g, 0.47 mmol) and potassium carbonate (3.90 g, 28.19 mmol) were dissolved in 90 mL of tetrahydrofuran / water (30 mL), and the mixture was refluxed with stirring for 12 hours. After the reaction was completed, the temperature was lowered to room temperature. Thereafter, the reaction mixture was extracted with water and methylene chloride, the solvent was removed, and column chromatography was performed under the condition of hexane: acetylacetate = 85:15 to obtain 4.85 g (69%) of Intermediate L2. The material was identified by HPLC analysis.

Synthesis of Compound 47

Intermediate L2 (1.59 g, 2.13 mmol), PtCl ₂ (NCPh) ₂ (1.11 g, 2.35 mmol) and 20 mL of benzonitrile were mixed and refluxed and stirred for 12 hours to lower the temperature to room temperature. After removing the solvent from the resulting mixture, column chromatography was performed under the condition of hexane: methylene chloride = 8: 2 to obtain 0.32 g (16%) of Compound 47. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₅₁ H ₄₂ N ₄ O ₂ Pt: m / z 937.2956, Found: 937.2950

Synthetic example  3: Synthesis of Compound 100

Synthesis of intermediate L3

Intermediate L3-1 (2.45 g, 5.98 mmol) , Intermediate L1-2 (2.65 g, 6.28 mmol) , Pd (PPh 3) 4 (0.35 g, 0.30 mmol) and potassium carbonate (2.48 g, 17.94 mmol) tetrahydro- The reaction mixture was stirred at reflux for 12 hours, and the reaction was allowed to proceed to room temperature. Thereafter, the reaction mixture was extracted with water and methylene chloride, the solvent was removed, and column chromatography was performed under the condition of hexane: acetylacetate = 85:15 to obtain 2.76 g (69%) of Intermediate L3. The material was identified by HPLC analysis.

Synthesis of Compound 100

Intermediate L3 (1.19 g, 1.60 mmol), PtCl ₂ (NCPh) ₂ (0.83 g, 1.76 mmol) and 15 mL of benzonitrile were mixed and refluxed and stirred for 8 hours before the temperature was lowered. The solvent was removed from the resulting mixture, and column chromatography was performed under the condition of hexane: methylene chloride = 8: 2 to obtain 0.41 g (27%) of Compound 100. Mass and HPLC analysis confirmed the material.

_{HRMS (MALDI) calcd for C 45} H 38 N 4 O 2 Pt: m / z 861.2643, Found: 861.2635

Synthetic example  4: Synthesis of compound 180

Synthesis of intermediate L4

Intermediate L3-1 (2.65 g, 6.49 mmol) , Intermediate L4-1 (2.52 g, 6.81 mmol) , Pd (PPh 3) 4 (0.38 g, 0.32 mmol) and potassium carbonate (2.69 g, 19.46 mmol) tetrahydro- The reaction mixture was stirred at reflux for 12 hours, and the reaction was allowed to proceed to room temperature. Thereafter, the reaction mixture was extracted with water and methylene chloride, the solvent was removed, and column chromatography was performed under the condition of hexane: acetylacetate = 85:15 to obtain 2.21 g (55%) of Intermediate L4. The material was identified by HPLC analysis.

Synthesis of compound 180

Intermediate L4 (1.90 g, 3.09 mmol), PtCl ₂ (NCPh) ₂ (1.60 g, 3.40 mmol) and 20 mL of benzonitrile were mixed and refluxed with stirring for 12 hours to allow the reaction to proceed to room temperature. After removing the solvent from the resulting mixture, column chromatography was performed under the condition of hexane: methylene chloride = 7: 3 to obtain 0.58 g (23%) of Compound 180. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₄₁ H ₃₄ N ₄ O ₂ Pt: m / z 809.2330, Found: 809.2338

Example  One

The ITO glass substrate was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, and then subjected to UV ozone cleaning for 30 minutes.

Then, m-MTDATA was deposited on the ITO electrode (anode) on the glass substrate at a deposition rate of 1 Å / sec to form a hole injection layer having a thickness of 600 Å, and α-NPD was deposited on the hole injection layer at a deposition rate of 1 Å / sec To form a hole transporting layer having a thickness of 250 ANGSTROM.

Compound 20 (dopant) and CBP (host) were co-deposited at a deposition rate of 0.1 Å / sec and 1 Å / sec, respectively, on the hole transporting layer to form a 400 Å thick light emitting layer.

Alq ₃ was deposited on the hole blocking layer to form an electron transporting layer having a thickness of 300 A, and then an electron transport layer having a thickness of 50 Å was formed on the electron transporting layer by depositing LiF M-MTDATA (600 Å) / α-NPD (600 Å) was formed by vacuum evaporation of Al on the electron injection layer to form a second electrode (cathode) (250 Å) / CBP + 10% (Compound 20) (400 Å) / Balq (50 Å) / Alq ₃ (300 Å) / LiF (10 Å) / Al (1200 Å).

Example  2 to 4 and Comparative Example  One

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound described in Table 2 was used instead of Compound 20 as a dopant in forming the light emitting layer.

Evaluation example  1: Evaluation of characteristics of organic light emitting device

The driving voltage, color purity, quantum efficiency and lifetime (T ₉₅ ) were evaluated for each of the organic light emitting devices manufactured in Examples 1 to 4 and Comparative Example 1, and the results are shown in Table 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as the evaluation device, and the life time (T ₉₅ ) (at 6000 nit) was evaluated to be 95% of the initial luminance 100%.

Dopant Driving
Voltage
(V) CIEx CIEy quantum
efficiency
(%) life span
(hr)
(T ₉₅ ) Example 1 Compound 20 5.1 0.628 0.356 16.5 140h Example 2 Compound 47 4.9 0.669 0.329 17.5 155h Example 3 Compound 100 4.4 0.519 0.472 18.3 255h Example 4 Compound 180 4.8 0.523 0.468 18.8 110h Comparative Example 1 Compound A 5.8 0.311 0.622 14.1 20h

<Compound A>

It can be seen from Table 2 that the organic light emitting devices of Examples 1 to 4 have improved driving voltage, quantum efficiency, and lifetime characteristics as compared with the organic light emitting device of Comparative Example 1. [

10: Organic light emitting device
11: first electrode
15: Organic layer
19: Second electrode

Claims (20)

An organometallic compound represented by the following formula (1):
&Lt; Formula 1 >

In the above formula
M is at least one selected from the group consisting of beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu) ), Germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt)
X ₁ is O or S, the bond between X ₁ and M is a covalent bond,
X ₂ is N, the bond between X ₂ and M is a coordination bond,
X ₃ and X ₄ independently of one another are C or N,
One of the bonds between X ₃ and M and the bond between X ₄ and M is a covalent bond and the other is a coordinate bond,
Y ₁ to Y ₇ are independently of each other C or N,
Y ₈ and Y ₉ are independently of each other C, N, O or S,
A bond between Y ₁ and Y ₈ or an atomic group and a bond or an atomic group between Y ₁ and Y ₂ constitute CY ₁ and a bond or an atomic group between X ₂ and Y ₃ and a bond or an atomic group between X ₂ and Y ₄ CY ₂ , the bond between X ₃ and Y ₅ or the atomic group and the bond or atomic group between X ₃ and Y ₆ constitute CY ₃ , the bond or atomic group between X ₄ and Y _7, and the bond between X ₄ and Y ₉ Or the atomic group constitutes CY ₄ ,
CY ₁ , CY ₃ and CY ₄ are each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group,
CY ₂ is a group selected from the group consisting of azacarbazole group, azadibenzo boro group, azadibenzophosphole group, azafluorene group, azadibenzosilyl group, azadibenzomol group, Azadibenzothiophene group, azadibenzoselenophen group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group and azadibenzothiophene 5,5 - &lt; / RTI &gt;
T ₁ to T ₃ independently of each _{other, * -N [(L 5)} a5 - (R 5)] - * ', * -B (R 5) - *', * -P (R 5) - * ' _{, * -C (R 5) (} R 6) - * ', * -Si (R 5) (R 6) - *', * -Ge (R 5) (R 6) - * ', * -S- * ', * -Se- *', * -O- * ', * -C (= O) - *', * -S (= O) - * ', * -S (= O) 2 - *' _{, * -C (R 5) =} * ', * = C (R 5) - *', * -C (R 5) = C (R 6) - * ', * -C (= S) - *' And * -C? C- * ',
L ₅ is selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
a5 is 1 to 3 selected from, a5, if 2 or more, two or more of L ₅ are the same or different from each other,
R ₅ and R ₆ are optionally linked to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,
b1 to b3 independently of one another are 0, 1, 2 or 3 and when b1 is 0, * - (T ₁ ) _b1 - * is a single bond, and when b2 is 0 * - (T ₂ ) _b2 - * is a single bond, and when b3 is 0, * - (T ₃ ) _{b 3} - * '
R ₁ to R ₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ arylox group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or non-substituted 1-aromatic-axis A polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q ₇ ) and -P (= O) (Q ₈ ) (Q ₉ )
a1 to a4 are independently of each other 0, 1, 2, 3, 4 or 5,
two of a1 of R ₁ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
two of a2 of R ₂ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
two of a3 of R ₃ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
two of a4 of R ₄ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
Two or more of the neighboring R ₁ to R ₄ may optionally be bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,
One of R ₅ and R ₆ and R ₃ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group You can,
R ₅ and R ₆ and R ₁ , R ₂ , R ₃ or R ₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ Lt; RTI ID = 0.0 &gt; C30 &lt; / RTI _&gt; heterocyclic group,
The substituted C ₅ -C ₃₀ carbocyclic group, a substituted C ₁ -C ₃₀ heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C _A substituted C ₁ -C ₆ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ cycloalkenyl group, -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, , The substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocyclic polycyclic group,
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group And a C ₁ -C ₆₀ alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, and C _A C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, - _{N (Q 21) (Q 22} ), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q 29) at least one selected from the substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ Group-, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );
&Lt; / RTI &gt;
Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ aryl A C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group. The method according to claim 1,
CY ₁ , CY ₃ and CY ₄ are independently selected from the group consisting of a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, Tetrahydronaphthalene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzo borole group, a benzofospor group, an indene group, a benzoylol group, , A benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzo borole group, a dibenzo phosphole group, a fluorene group, a dibenzoylsilole group, a dibenzothymol group, Dibenzothienophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azacavazole group, azadibenzoporone Group, azadibenzophosphole group, azafluorene group, azadiene group, Azaindibenzothiophene group, azadibenzoselenophen group, azadibenzofurane group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one A pyridine group, a pyridazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, Group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group , Benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline ) Group and 5,6,7,8-tetrahydroquinoline (5,6,7,8-te trahydroquinoline. &lt; / RTI &gt; The method according to claim 1,
T ₁ to T ₃ independently of each _{other, * -N [(L 5)} a5 - (R 5)] - * ', * -C (R 5) (R 6) - *', * -Si (R 5 ) (R ₆ ) - * ', * -S- *' and * -O- * '. The method according to claim 1,
T ₁ to T ₃ independently of each _{other, * -C (R 5) (} R 6) - * ', * -Si (R 5) (R 6) - *' and _{* -Ge (R 5) (R} 6 ) - * &apos;,&lt; / RTI &gt;
And R ₅ and R ₆ are connected to each other through a first connector,
The first connector is a single _{bond, * -N [(L 9)} a9 - (R 9)] - * ', * -B (R 9) - *', * -P (R 9) - * ', _{* -C (R 9) (R} 10) - * ', * -Si (R 9) (R 10) - *', * -Ge (R 9) (R 10) - * ', * -S- * ', * -Se- *', * -O- * ', * -C (= O) - *', * -S (= O) - * ', * -S (= O) 2 - *', _{* -C (R 9) = *} ', * = C (R 9) - *', * -C (R 9) = C (R 10) - * ', * -C (= S) - *' and * -C? C- * ',
The description of R &lt; ₉ &gt; and R &lt; ₁₀ &gt; refer to the description of R &lt; ₅ &
For a description of L ₉ , refer to the description of L ₅ in the first paragraph,
The description of a9 refers to the description of a5 in the first paragraph,
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
b1, b2 and b3 are 0;
b1 is 1, b2 and b3 are 0;
b2 is 1, b1 and b3 are 0; or
b3 is 1, b1 and b2 are 0; Organometallic compounds. The method according to claim 1,
R ₁ to R ₆ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, An adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one;
A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A phenyl group, a pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, an imidazolyl group, an imidazolyl group, a pyrazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, A quinolinyl group, a quinolizinyl group, a quinazolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazole group, a benzoquinolyl group, a benzoquinolinyl group, A benzooxazolyl group, a benzoxazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyridinyl group, A diazopyrimidinyl group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, A cycloheptenyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a naphthyl group, a naphthyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, , Isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, , An indolyl group, an indolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, A benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofurano group, A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group substituted with at least one member selected from a phenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group a cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthene group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyrimidyl group, a pyridyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, A benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And
_{-N (Q 1) (Q 2} ), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );
&Lt; / RTI &gt;
Q ₁ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt; The method according to claim 1,
R ₁ to R ₆ are, independently of each other,
An alkyl group having 1 to 10 carbon atoms which may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , methyl, ethyl, n-propyl, isopropyl, An n-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an isobutyl group, an isobutyl group, , a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secononyl group, A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, A norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, A dibenzothiophenyl group;
Heavy _{hydrogen, -F, -CD 3, -CD 2} H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, cyano, nitro, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy A cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, An ethyl group, an n-propyl group, an isopropyl group, an isopropyl group, an isopropyl group, a n-butyl group, a n-butyl group, a n-butyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, A tert-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, heptyl group, n-octyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, isohexyl group, , sec-nonyl group, tert-nonyl group, n- A cyclohexyl group, a cycloheptyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzyl group, a naphthyl group, A benzofuranyl group and a dibenzothiophenyl group; And
_{-N (Q 1) (Q 2} ), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );
&Lt; / RTI &gt;
Q ₁ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt; The method according to claim 1,
R ₁ to R ₆ independently represent hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , CF ₂ H, -CFH _2, the following formulas 9-1 to 9-19 group, the following formulas 10-1 to groups and _{-Si (Q 3) (Q 4} ) represented by the 10-142 represented by (Q ₅₎ : &Lt; / RTI &gt;

In the above formulas (9-1) to (9-19) and (10-1) to (10-142), * denotes a binding site with neighboring atoms, Ph denotes a phenyl group, and TMS denotes a trimethylsilyl group. The method according to claim 1,
In the above formula

Is an organometallic compound selected from the group consisting of the following chemical formulas CY1-1 to CY1-16:

Among the above-mentioned formulas CY1-1 to CY1-16
And X ₁₁ is N or C (R _11), X ₁₂ is N or C (R _12), and, X ₁₃ is N or C (R _13), and, X ₁₄ is N or C (R _14), X ₁₅ a is N or C (R _15), and, X ₁₆ is N or C (R _16), and, X ₁₇ is N or C (R _17), and, X ₁₈ is N or C (R _18),
X ₁₉ is C (R _19a ) (R _19b ), N (R ₁₉ ), O, S or Si (R _19a ) (R _19b )
R ₁₁ to R ₁₉ and R _19a to R _19c independently of each other refer to the description of R ₁ in the first paragraph,
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

Is an organic metal compound selected from the group consisting of the following chemical formulas CY2-1 to CY2-4:

Among the above-mentioned formulas CY2-1 to CY2-4
And X ₂₁ is N or C (R _21), X ₂₂ is N or C (R _22), and, X ₂₃ is N or C (R _23), and, X ₂₄ is N or C (R _24), and, X ₂₅ Is N or C (R &lt; ₂₅ &gt;),
X ₂₉ is C (R _29a ) (R _29b ), N (R ₂₉ ), O, S or Si (R _29a ) (R _29b )
R ₂₁ to R ₂₅ , R ₂₉ and R _29a to R _29c independently of each other refer to the description of R ₂ in the first paragraph,
*, *, And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

Is an organic metal compound selected from the group consisting of the following chemical formulas CY3-1 to CY3-22:

Among the above-mentioned formulas CY3-1 to CY3-22
And X ₃₁ is N or C (R _31), X ₃₂ is N or C (R _32), and, X ₃₃ is N or C (R _33), and, X ₃₄ is N or C (R _34), and, X ₃₅ Is N or C (R ₃₅ ), X ₃₆ is N or C (R ₃₆ ), X ₃₇ is N or C (R ₃₇ )
X ₃₉ is a _{C (R 39a) (R 39b} ), N (R 39), O, S , or _{Si (R 39a) (R 39b} ),
R ₃₁ to R ₃₉ and R _39a to R _39b independently of one another refer to the description of R ₃ in the first paragraph,
*, *, And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

, Wherein the moiety is selected from the group consisting of the following formulas CY4-1 to CY4-8,

Among the above-mentioned formulas CY4-1 to CY4-8
And X ₄₁ is N or C (R _41), X ₄₂ is N or C (R _42), and, X ₄₃ is N or C (R _43), and, X ₄₄ is N or C (R _44), X ₄₅ Is N or C (R ₄₅ ), X ₄₆ is N or C (R ₄₆ ), X ₄₇ is N or C (R ₄₇ ), X ₄₈ is N or C (R ₄₈ )
The description of R ₄₁ to R ₄₈ independently of each other, with reference to the description of R ₄ in the first paragraph,
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
CY1 is selected from the group consisting of the following formulas CY1 (1) to CY1 (9)
CY2 is selected from the group consisting of the following formulas CY2-1 to CY2-4,
CY3 is selected from the group consisting of the following formulas CY3 (1) to CY3 (14)
CY4 is an organometallic compound selected from the group consisting of the following chemical formulas CY4 (1) to CY4 (9)

The description of R ₁₁ to R ₁₄ in the above formulas CY1 (1) to CY1 (9) will be described with reference to the description of R ₁ in the first paragraph, wherein R ₁₁ to R ₁₄ are not hydrogen,
And X ₂₁ is N or C (R ₂₁₎ In the formula CY2-1 to CY2-4, X ₂₂ is N or C (R _22), and, X ₂₃ is C (R _23), and, X ₂₄ is C (R ₂₄ ), X ₂₅ is C (R ₂₅ )
X ₂₉ is C (R _29a ) (R _29b ), N (R ₂₉ ), O, S or Si (R _29a ) (R _29b )
R ₂₁ to R ₂₅ , R ₂₉ and R _29a to R _29c independently of each other refer to the description of R ₂ in the first paragraph,
In the formula, CY3 (1) to CY3 (14) X ₃₉ are _{C (R 39a) (R 39b} ), N (R 39), O, S , or _{Si (R 39a) (R 39b} ) , and, R ₃₁ to R ₃₃ , R ₃₉ , R _39a and R _39b are each as described in the description of R ₃ in the first paragraph, wherein R ₃₁ to R ₃₃ are not hydrogen,
The description of R ₄₁ to R ₄₄ in the above formulas CY4 (1) to CY4 (9) will be described with reference to the description of R ₄ in the first paragraph, wherein R ₄₁ to R ₄₄ are not hydrogen,
*, * And * in the above formulas CY (1) to CY (9), CY2-1 to CY2-4, CY3 (1) to CY3 (14) and CY4 It is a binding site with one atom. The method according to claim 1,
An organometallic compound represented by one of the following formulas (1) and (2):

In the above formulas (1) and (2)
The descriptions of M, X ₁ to X ₄ , Y ₁ to Y ₉ , CY ₁ to CY ₄ , T ₁ to T ₃ , b ₁ to b ₃ , R ₁ to R ₄ and a ₁ to a ₄ are as described in Referring to the bar,
X ₄₂ is N or C (R ₄₂ ), X ₄₃ is N or C (R ₄₃ ), X ₄₄ is N or C (R ₄₄ )
R ₄₂ to R ₄₄ independently of each other refer to the description of R ₄ in the first paragraph and two of R ₄₂ to R ₄₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ - C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
CY ₅ and CY ₆ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
R ₅₁ and R ₆₁ are independently of each other, with reference to the description of R ₁ in the first paragraph,
a51 and a61 are, independently of each other, 0, 1, 2 or 3,
T ₄ is C, Si or Ge,
T ₅ is a single _{bond, * -N [(L 7)} a7 - (R 7)] - * ', * -B (R 7) - *', * -P (R 7) - * ', * -C _{(R 7) (R 8)} - * ', * -Si (R 7) (R 8) - *', * -Ge (R 7) (R 8) - * ', * -S- *', * -Se- * ', * -O- *' , * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C _{(R 7) = * ',} * = C (R 7) - *', * -C (R 7) = C (R 8) - * ', * -C (= S) - *' and * -C ≡C- * ',
The description of R ₇ and R ₈ is the same as the description of R ₅ in the first embodiment,
L ₇ refers to the description of L ₅ in the first paragraph,
a7 refers to the description of a5 in the first paragraph,
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
An organometallic compound selected from the following compounds 1 to 240:

A first electrode;
A second electrode; And
An organic layer interposed between the first electrode and the second electrode, the organic layer including a light emitting layer;
/ RTI &gt;
Wherein the organic layer contains at least one organometallic compound of any one of claims 1 to 15. 17. The method of claim 16,
Wherein the first electrode is an anode,
The second electrode is a cathode,
Wherein the organic layer further comprises a hole transporting region interposed between the first electrode and the light emitting layer and an electron transporting region interposed between the light emitting layer and the second electrode,
Wherein the hole transporting region comprises a hole injecting layer, a hole transporting layer, an electron blocking layer or any combination thereof,
Wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. 17. The method of claim 16,
Wherein the organic metal compound is contained in the light emitting layer. 19. The method of claim 18,
Wherein the light emitting layer further comprises a host, and the content of the host is larger than the content of the organometallic compound. A diagnostic composition comprising at least one organometallic compound according to any one of claims 1 to 15.

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